2-Ethoxyphenethylamine → (2S)-2-ethoxy-3-(4-{1-[2-(2-ethoxy-phenyl)-ethylcarbamoyl]-1-methyl-ethoxy}-phenyl)-propionic acid

HRID 1353260Notes

Reaction equation

HRID 1353260 reaction equation
C([O:3][C:4](=[O:23])[C@@H:5]([O:20][CH2:21][CH3:22])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([C:17]([OH:19])=O)([CH3:16])[CH3:15])=[CH:9][CH:8]=1)C.[CH2:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][CH2:34][NH2:35])[CH3:25].C(O[C@@H](CC1C=CC(O[C@@H](C(=O)NCCC2C=CC(OC3C=CC=CC=3)=CC=2)C)=CC=1)C(O)=O)C>>[CH2:21]([O:20][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]([C:17](=[O:19])[NH:35][CH2:34][CH2:33][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH2:24][CH3:25])([CH3:15])[CH3:16])=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 1423622-EthoxyphenethylamineHCID 9847886(2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)propionic acidHCID 58646608(2S)-3-[4-(1-carboxy-1-methyl-ethoxy)-phenyl]-2-ethoxy-propionic acid ethyl ester

Product 1

HCID 10072109(2S)-2-ethoxy-3-(4-{1-[2-(2-ethoxy-phenyl)-ethylcarbamoyl]-1-methyl-ethoxy}-phenyl)-propionic acid

Procedure

The title compound was prepared from (2S)-3-[4-(1-carboxy-1-methyl-ethoxy)-phenyl]-2-ethoxy-propionic acid ethyl ester (EXAMPLE 49, step 2) and 2-(2-ethoxy-phenyl)-ethylamine via the same procedure used for the preparation of (2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)-propionic acid (Example 1, step 3) to produce a colorless oil. MS (ES) for C25H33NO6 [M+H]+: 444.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-16538aaa15d14b7eb2643aa049ba2878
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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